Toluene → HCID 178448141, compound

HRID 1695012Notes

Reaction equation

HRID 1695012 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1.O[CH2:21][C@H:22]([NH:32][S:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[N+:42]([O-:44])=[O:43])(=[O:35])=[O:34])[C@@H:23]1[CH2:27][C@@H:26]([CH2:28][CH2:29][CH3:30])[C:25](=[O:31])[O:24]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[N+:42]([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[S:33]([N@:32]1[CH2:21][CH:22]1[C@H:23]1[O:24][C:25](=[O:31])[C@H:26]([CH2:28][CH2:29][CH3:30])[CH2:27]1)(=[O:35])=[O:34])([O-:44])=[O:43]

Participants

6

Reactant 4

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66645749N-{(S)-2-hydroxy-1-[(2S,4R)-5-oxo-4-propyltetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamide

Product 1

HCID 178448141HCID 178448141, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.95 ml of a solution of diethyl azodicarboxylate in toluene (40%) (6.48 mmol) was added to a solution of 2.01 g of N-{(S)-2-hydroxy-1-[(2S,4R)-5-oxo-4-propyltetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamide obtained in Example (116f) (5.4 mmol) and 1.7 g of triphenylphosphine (6.48 mmol) in tetrahydrofuran (54 ml) under ice-cooling over five minutes, and the mixture was stirred at the same temperature for 10 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: toluene/acetone=5/1) to obtain 1.4 g of the title compound (yield: 74%).

Workup

  1. temperaturecooling over five minutes
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (elution solvent: toluene/acetone=5/1)

Sources & evidence

ORD record
ord-c97e2292836f467faa839cdab7327411
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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